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Introduction: The passage from adolescence to young adulthood introduces many challenges and chances aimed at promoting independence, financial self-sufficiency, assumption of responsibilities and separation from parents. Literature shows that in the continuum between these two phases of life, many factors intervene, producing significant differentiations. Methods: This study considered three dimensions - well-being, measured through the Clinical Outcomes in Routine Evaluation-Outcome Measure (CORE-OM); spontaneity, measured through the Spontaneity Assessment Inventory-Revised (SAI-R); and self-efficacy, measured through the General Self-Efficacy scale (GSE). The study involved two groups of Italian participants: 495 adolescents, aged between 13 and 19 years, selected at a high school; and 368 young adults, aged between 18 and 30 years, recruited by snowball sampling. Results: Results of confirmatory factor analysis for each instrument in each group indicate the validity of the three instruments for both age groups. No significant differences were found between adolescents and young adults on total or subtotal scores of the CORE-OM, except for the risk factor. Conversely, the mean scores obtained with SAI-R and GSE were very different between adolescents and young adults. Conclusions: The results of path analysis show a significant mediation of spontaneity in the link between self-efficacy and all specific psychological distress domains for adolescents. Instead, there is a significant mediation of spontaneity between self-efficacy and all specific psychological distress domains except the risk domain for young adults.